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The Cheshire Cat is unique among Wonderland creatures. Threatened by no one, it maintains a cool, grinning outsider status. The Cheshire Cat has insight into the workings of Wonderland as a whole. Its calm explanation to Alice that to be in Wonderland is to be “mad” reveals a number of points that do not occur to Alice on her own. First, the Cheshire Cat points out that Wonderland as a place has a stronger cumulative effect than any of its citizens. Wonderland is ruled by nonsense, and as a result, Alice’s normal behavior becomes inconsistent with its operating principles, so Alice herself becomes mad in the context of Wonderland. Certainly, Alice’s burning curiosity to absorb everything she sees in Wonderland sets her apart from the other Wonderland creatures, making her seem mad in comparison.
Although the Cheshire Cat understands the madness of Wonderland in ways that other creatures in the book do not, it doesn’t condemn that madness. Rather, it embraces its own insanity, and the insanity of those around it, seeing madness not as a negative trait but rather as a natural state of existence. Its cool, collected nature challenges Alice’s assumptions about what it means to be insane. The Cheshire Cat’s characterization of madness suggests that madness is not necessarily simply being nonsensical or silly, but rather thinking and behaving in ways that diverge from cultural norms and expectations. Menacing, intelligent, and mischievous all at once, the Cheshire Cat demands Alice’s respect in ways the other creatures of Wonderland do not, and despite its self-admitted madness, Alice mostly refrains from imposing her own worldview or logic on it as she does with other characters throughout the novel.
